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Metal- and solvent-free synthesis of aniline- and phenol-based triarylmethanes via Bronsted acidic ionic liquid catalyzed Friedel-Crafts reaction.

ABSTRACT: A beneficial, scalable and efficient methodology for the synthesis of aniline-based triarylmethanes has been established through the double Friedel-Crafts reaction of commercial aldehydes and primary, secondary or tertiary anilines using Brönsted acidic ionic liquid as a powerful catalyst, namely [bsmim][NTf₂]. This protocol was successfully performed under metal- and solvent-free conditions with a broad range of substrates, giving the corresponding aniline-based triarylmethane products in good to excellent yields (up to 99%). In addition, alternative aromatic nucleophiles such as phenols and electron-rich arenes were also studied using this useful approach to achieve a diversity of triarylmethane derivatives in high to excellent yields.

SUBMITTER: Ponpao N

PROVIDER: S-EPMC9034371 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Metal- and solvent-free synthesis of aniline- and phenol-based triarylmethanes via Brönsted acidic ionic liquid catalyzed Friedel-Crafts reaction.

Ponpao Nipaphorn N Senapak Warapong W Saeeng Rungnapha R Jaratjaroonphong Jaray J Sirion Uthaiwan U

RSC advances 20210630 37

A beneficial, scalable and efficient methodology for the synthesis of aniline-based triarylmethanes has been established through the double Friedel-Crafts reaction of commercial aldehydes and primary, secondary or tertiary anilines using Brönsted acidic ionic liquid as a powerful catalyst, namely [bsmim][NTf2]. This protocol was successfully performed under metal- and solvent-free conditions with a broad range of substrates, giving the corresponding aniline-based triarylmethane produc ...[more]

PMID: 35480415

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